Acetophenone → HCID 10426365, compound

HRID 1198031Notes

Reaction equation

HRID 1198031 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])[CH3:14].[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]([CH3:33])[CH3:32])[C:26]=1[N:34]=[C:35]=[O:36])([CH3:24])[CH3:23]>CCOCC>[CH3:24][CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]([CH3:32])[CH3:33])[C:26]=1[NH:34][C:35](=[O:36])[CH2:14][C:13](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:23]

Participants

6

Reactant 4

HCID 7410AcetophenoneHCID 7912DiisopropylamineHCID 922592,6-Diisopropylphenyl isocyanateHCID 178418339Butyllithium

Product 1

HCID 10426365HCID 10426365, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Conditions

Temperature
-78 °C

Procedure

To a cooled (-78° C.) solution of diisopropylamine (2.48 g, 0.024 mol) in 100 mL ether, n-BuLi (0.024 mol) was added dropwise followed by 50 mL ether. After stirring for 5 minutes at -78° C. under a nitrogen atmosphere, a solution of acetophenone (2.95 g, 0.024 mol) in 25 mL ether was added dropwise and the resulting solution was stirred for 20 minutes at -78° C. A solution of 2,6-diisopropylphenyl isocyanate in 25 ML Et2O was then added dropwise and the reaction mixture was allowed to gradually warm to room temperature and stir for 16 hours under a nitrogen atmosphere (J. F. Wolfe, et al, Synthetic Communications 17, 13 (1987)). The reaction mixture was then quenched with a saturated solution of ammonium chloride and extracted with methylene chloride. The layers were separated and the organic layer was washed two times with water, dried (Na2SO4) and concentrated in vacuo (30° C.) to afford a yellow residue. This residue was washed with hexane, filtered, and oven-dried (40° C.) to yield a pale yellow solid, 4.3 g (0.013 mol, 54%) of the title compound, mp 124°-126° C.

Workup

  1. additionwas added dropwise
  2. stirringthe resulting solution was stirred for 20 minutes at -78° C
  3. temperatureto gradually warm to room temperature
  4. stirringstir for 16 hours under a nitrogen atmosphere (J. F. Wolfe, et al, Synthetic Communications 17, 13 (1987))
  5. customThe reaction mixture was then quenched with a saturated solution of ammonium chloride
  6. extractionextracted with methylene chloride
  7. customThe layers were separated
  8. washthe organic layer was washed two times with water
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo (30° C.)
  11. customto afford a yellow residue
  12. washThis residue was washed with hexane
  13. filtrationfiltered
  14. customoven-dried (40° C.)

Sources & evidence

ORD record
ord-3d6683e2fdd247f3b7fcdf00c10cc2f1
Source dataset
uspto-grants-1994_01
Patent number
US05278326

Reaction notes

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